CN1172614A - Antioxidant composition and method for production thereof - Google Patents
Antioxidant composition and method for production thereof Download PDFInfo
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- CN1172614A CN1172614A CN97113025A CN97113025A CN1172614A CN 1172614 A CN1172614 A CN 1172614A CN 97113025 A CN97113025 A CN 97113025A CN 97113025 A CN97113025 A CN 97113025A CN 1172614 A CN1172614 A CN 1172614A
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- ultimate density
- antioxidant composition
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/34—Anti-oxidant compositions; Compositions inhibiting chemical change containing plant or animal materials of unknown composition
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3472—Compounds of undetermined constitution obtained from animals or plants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Botany (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Food Science & Technology (AREA)
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- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nutrition Science (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Fats And Perfumes (AREA)
Abstract
Th present invention relates to an antioxidant composition which can be obtained efficiently at high yields by(a)adding ethanol to a hot water fraction of an oyster meat to a final concentration of not less than 40(w/w)% to obtain a supernatant(step 1),(b)concentrating the obtained supernatant to a solid content of 30-45(w/w)%(step 2), and(c)adding ethanol thereto to a final concentration of 55-70(w/w)% to recover precipitates(step 3).
Description
The present invention relates to a kind of antioxidant composition that derives from the Oyster hot water extract and preparation method thereof.
Can produce when oxygen is exposed to ultraviolet ray or radiation and have the supervirulent ultra-oxygen anion free radical that is called as active oxygen.It is converted into hydrogen peroxide or hydroxyl radical free radical and causes multiple oxidation disorder in human body.It is believed that described mechanism can cause multiple diseases such as comprising aging and tumour formation.
Oxidation inhibitor enzyme in the human body such as superoxide-dismutase (SOD) and oxidation inhibitor material more and more are considered to can be to the disorderly protection biology that plays key of this oxidation.In addition, form the focus of noting for people by the oxidation inhibitor material of taking in the food because of its potential vital role in pre-anti-oxidation disorder.
In addition, owing to contain a large amount of taurines, glycogen, protein and other can utilize material, Oyster is also referred to as " milk in the sea " (milk in the sea).
To the research of Oyster composition with the survey showed that, alcohol concn and solids content can obtain containing the highly purified superior antioxidant composition that derives from Oyster between the ethanol separation period by adjusting according to the present invention.
Therefore, the invention provides following content.(1) a kind of method for preparing antioxidant composition is comprising following steps: (a) add ethanol with the ultimate density that is not less than 40 (w/w) % in the hot water isolate of Oyster and obtain supernatant liquor (step 1); (b) with the gained supernatant concentration to containing 30-45 (w/w) % solids component (step 2); Reaching (c) is that 55-70 (w/w) % is to reclaim throw out (step 3) to wherein adding ethanol to ultimate density.(2) method of above-mentioned (1) is comprising step (c) is preceding to transfer to supernatant liquor pH below 3 or 3 carrying out.(3) method of above-mentioned (1) or (2), it satisfies at least one following requirement: (i) the alcoholic acid ultimate density is 40-50 (w/w) % in step 1, (ii) solid component content is 35-40 (w/w) % in step 2, and (iii) in the step 3 the alcoholic acid ultimate density be about 60 (w/w) %.(4) a kind of antioxidant composition is characterized in that having following characteristics: the material that (i) contains molecular weight and be 1000-5000 is UV absorption spectrum (see figure 1) λ (ii)
Max(aqueous solution): 267.5nm and 198nm be ninhydrin reaction (iii): the positive is main component (iv): (v) solvability: water-soluble (vi) color: the antioxidant composition of burgundy (5) above-mentioned (4) wherein prepares according to the method that comprises the steps low molecular weight peptide: (a) add ethanol with the ultimate density that is not less than 40 (w/w) % in the hot water isolate of Oyster and obtain supernatant liquor (step 1); (b) with the gained supernatant concentration to containing 30-45 (w/w) % solids component (step 2); Reaching (c) is that 55-70 (w/w) % is to reclaim throw out (step 3) to wherein adding ethanol to ultimate density.(6) antioxidant composition of above-mentioned (5) wherein prepares the pH of supernatant liquor carrying out the preceding method that transfers to below 3 or 3 of step (c) by further comprising.(7) antioxidant composition of above-mentioned (5) or (6), it satisfies at least one following requirement: (i) the alcoholic acid ultimate density is 40-50 (w/w) % in step 1, (ii) solid component content is 35-40 (w/w) % in step 2, and (iii) in the step 3 the alcoholic acid ultimate density be about 60 (w/w) %.
Fig. 1 is the UV absorption spectrum of antioxidant composition of the present invention.
In the present invention, for example, obtain the hot water parting liquid that supernatant prepares oyster meat by in oyster meat, adding hot water and removing sediment. In the present invention, as the oyster meat of starting material, as long as can keep above-mentioned antioxidant active, be not subjected to special restriction at it in form, and can be powder that give birth to, freezing or that prepare by drying and the oyster meat that grinds. The temperature that hot water separates the hot water that uses is generally 90 ℃ of 50-, and preferably about 70-80 ℃, extraction time is generally 2 to 3 hours.
Because described supernatant liquor generally contains the solids component of the 4-5 that has an appointment (w/w) %, preferably solid component content is transferred to 20-40 (w/w) % by concentrating.Deviate from this scope then precipitating proteins, carbohydrate etc. effectively.
Known ethanol can be by changing solvent polarity, promptly by changing hydrophobic and hydrophilicity causes precipitation.
In step 1 of the present invention, separate the supernatant liquor that obtains with extraction using alcohol by hot water, the alcoholic acid ultimate density is not less than 40 (w/w) %, preferably about 40-50 (w/w) %.When the alcoholic acid ultimate density is lower than 40 (w/w) %, can not fully separate active high molecular weight protein and the carbohydrate that is not needed of oxidation inhibitor.In addition, the gained supernatant liquor almost is identical with sedimentary oxidation inhibitor activity.When ultimate density surpassed 50 (w/w) %, the isolating effect of ethanol reached capacity.Disengaging time was generally 1-24 hour, preferred 5-12 hour.
In step 2 of the present invention, different solids contents has caused different Intermolecular Forcess.Stronger or more weak intermolecular combination brings different precipitations.When solids content reduced, ionization power reduces just to produce hanged down Intermolecular Forces and more a spot of precipitation.In step 2 of the present invention, will be 30-45 (w/w) % by the isolating supernatant concentration of above-mentioned ethanol to solids content, preferred 35-40 (w/w) %.When solids content was lower than 30 (w/w) %, precipitation capacity reduced, so sedimentary oxidation inhibitor activity also reduces.When solids content is higher than 45 (w/w) %, contain the active unwanted impurity of oxidation inhibitor in the precipitation, sedimentary specificity oxidation inhibitor is active to be reduced.By, method such as for example, heating concentrates, film oozes concentrated, freeze concentration is with supernatant concentration, and preferred especially decompression heating down concentrates.Measure solids content by the manual refractometer that uses Brix instrument such as Atago Corp to make with Brix (sugared concentration) expression.
The pH of above-mentioned concentrated liquid is transferred to below 3 or 3 preferred about 3.Generally regulate pH by adding sour example hydrochloric acid and Citric Acid.Protein and peptide precipitate under the isoelectric pH condition easily, when pH is higher than 3, cause precipitation capacity to reduce.
Behind the pH regulator, add ethanol in above-mentioned solution, making the alcoholic acid ultimate density is 55-70 (w/w) %, preferred about 60 (w/w) %, and the mixture centrifugation reclaimed throw out.Described throw out contains high density and has the active antioxidant composition of oxidation inhibitor.When the alcoholic acid ultimate density was lower than 55 (w/w) %, the productive rate of antioxidant composition reduced, and made the oxidation inhibitor activity between gained precipitation and the supernatant liquor almost not have difference.When it was higher than 70 (w/w) %, precipitation capacity increased, and unwanted pollutent also increases simultaneously, and specificity oxidation inhibitor activity becomes bad.
The antioxidant composition that obtains so also has following character except that its oxidation inhibitor activity: the material that (i) contains molecular weight and be 1000-5000 is UV absorption spectrum (see figure 1) λ (ii)
Max(aqueous solution): 267.5nm, 198nm is ninhydrin reaction (iii): the positive is main component (iv): low molecular weight peptide (v) solvability: water-soluble (vi) color: burgundy
Determine above-mentioned character by currently known methods.Specifically, according to adding ethanol sedimentary appearance or molecular weight do not occur inferring when separating.Measure UV spectrum with absorptiometry instrument commonly used.According to solubleness and the color in the method observation water of Japanese Pharmacopoeia (Japanese Pharmacopoeia) regulation.Can determine main component by the special color reaction of each component, the conventional qualitative and quantitative reaction of using.Ninhydrin reaction can be determined protein, polypeptide, amino acid etc., and can determine the existence of peptide by high performance liquid chromatography.
Describe the present invention in more detail by embodiment, and should not regard limitation of the present invention as.Embodiment 1
Water (50g) is added in the refrigerated Concha Ostreae (50g), and mixture was carried out hot water extraction in 2-3 hour 80-90 ℃ of heating, with 1500rpm (Hitachi, Ltd.) centrifugal 10 minutes.Is 20 to 40 (w/w) % by heating with gained supernatant concentration to solids content.Add ethanol with ultimate density 40 (w/w) % in the gained concentrated liquid, place after 12 hours, centrifugal (Hitachi Ltd.) obtained a kind of supernatant liquor (step 1) in 10 minutes with 3000rpm with mixture.Using rotatory evaporator to heat concentrating under reduced pressure supernatant liquor to solids content down at 50 ℃ is 37 (w/w) % (step 2).In the gained supernatant liquor, add 0.1M hydrochloric acid and regulate pH to 3.In described solution, add ethanol, regulate solids concn and pH therebetween to ultimate density 60 (w/w) %.Place after 12 hours, (Hitachi is Ltd.) with centrifugal 10 minutes throw out (step 3) with the form collection gained of antioxidant composition of mixture with 3000rpm.Detect the sedimentary character of gained according to following steps: (i) according to the following fact: separate the supernatant liquor that the hot water extract through 40 (w/w) % ethanol separation Oyster obtains with 60 (w/w) % ethanol and make throw out, infer that this fraction contains the material that a large amount of molecular weight are 1000-5000.(ii) the sedimentary sub-fraction of gained is dissolved in the water and measures its UV absorption spectrum with UV-2400PC (SHIMADZUCORPORATION) in a small amount.The results are shown in Figure 1.The result shows that absorption peak is positioned at 267.5nm and 198nm.(iii) the sedimentary sub-fraction of gained is dissolved in the water and adds ninhydrin reagent (0.2g is dissolved in the triketohydrindene hydrate in the 10ml water) in a small amount.Be heated and cool off, produce royal purple (positive) colour-change.(iv) under following condition, carry out high performance liquid chromatography and detect absorption peak, therefore determine the existence of peptide.Condition: post: Shodex Asahipak ODP-50 6E elutriant: 0.1M sodium perchlorate+0.1% sodium phosphate buffer (pH2)/acetonitrile=90/10
0.1M sodium perchlorate+0.1% sodium phosphate buffer (pH2)/acetonitrile=60/40
60 minutes flow velocity: 1.0ml/ minute detector: SPD-10A (SHIMADZU CORPORATION) of linear gradient elution column temperature: 30 ℃ (are v) detected the solvability in water and determine color on blank sheet of paper in room temperature.The result shows that this is precipitated as water miscible, and color is a burgundy.
The above results conforms to the character of above-mentioned antioxidant composition.Embodiment 2
Repeat the step identical with embodiment 1, different is in step 2 solids content to be transferred to 45 (w/w) %, obtains throw out thus.The gained throw out has identical character with above-mentioned antioxidant composition.Embodiment 3
Repeat the step identical, behind adjusting solids content that different is in step 3 and the pH, ethanol is added this solution to ultimate density 70 (w/w) %, obtain throw out thus with embodiment 1.The gained throw out has identical character with above-mentioned antioxidant composition.The comparative example 1
Repeat the step identical with embodiment 1, different is not add ethanol in the hot water separation of supernatant of Oyster in step 1, obtains throw out thus.The comparative example 2
Repeat the step identical with embodiment 1, different is in step 2 solids content to be adjusted to 18.5 (w/w) %, obtains throw out thus.The comparative example 3
Repeat the step identical, behind adjusting solids content that different is in step 3 and the pH, ethanol is added this solution to ultimate density 80 (w/w) %, obtain throw out thus with embodiment 1.Experimental example 1: detect the oxidation inhibitor activity
Detect every 100g Oyster hot water extract obtains among embodiment 1 to 3 and the comparative example 1 to 3 throw out amount and this sedimentary oxidation inhibitor activity.In this experimental example, by measuring the eliminate activity of active oxygen (superoxide anion) is measured the oxidation inhibitor activity, this detection is carried out according to spectrum catching method (ESR spin trap method).This spectrum catching method comprises the reaction of a kind of extremely unsettled free radical and capture agent to detect metastable free radical.In this experimental example, active oxygen result from xanthine-xanthine oxidase system and with DMPO (5,5-dimethyl-1-pyrroles-1-oxide compound, 5,5-dimethyl-1-pyrrollen-1-Oxide) detect as spin trapping reagent.Eliminating 50% active oxygen that produces (is IC
50) sample size that needs is taken as the eliminate activity to active oxygen, i.e. oxidation inhibitor activity.Less IC
50Show stronger oxidation inhibitor activity.The results are shown in Table 1.
Table 1
| Precipitation (g) | Oxidation inhibitor activity (IC 50) ????(μg) | |
| Embodiment 1 | ????1.5 | ????0.035 |
| Embodiment 2 | ????1.5 | ????0.030 |
| Embodiment 3 | ????1.6 | ????0.041 |
| The comparative example 1 | ????56.2 | ????0.579 |
| The comparative example 2 | ????1.9 | ????0.066 |
| The comparative example 3 | ????2.5 | ????0.090 |
According to the present invention, can be by obtaining highly purified antioxidant composition with high-level efficiency and high yield among the hot water extract of Oyster.
This application is based on Japanese patent application 115135/1996, and its content is incorporated herein for reference.
Claims (7)
1. method for preparing antioxidant composition is comprising following steps: (a) add ethanol with the ultimate density that is not less than 40 (w/w) % in the hot water isolate of Oyster and obtain supernatant liquor (step 1); (b) with the gained supernatant concentration to containing 30-45 (w/w) % solids component (step 2); Reaching (c) is that 55-70 (w/w) % is to reclaim throw out (step 3) to wherein adding ethanol to ultimate density.
2. the described method of claim 1 is comprising step (c) is preceding to transfer to pH below 3 or 3 carrying out.
3. claim 1 or 2 described methods, it satisfies at least one following requirement: (i) the alcoholic acid ultimate density is 40-50 (w/w) % in step 1, (ii) solid component content is 35-40 (w/w) % in step 2, and (iii) alcoholic acid ultimate density about 60 (w/w) % in the step 3.
4. antioxidant composition is characterized in that having following character: the material that (i) contains molecular weight and be 1000-5000 is UV absorption spectrum (see figure 1) λ (ii)
Max(aqueous solution): 267.5nm and 198nm be ninhydrin reaction (iii): the positive is main component (iv): low molecular weight peptide (v) solvability: water-soluble (vi) color: burgundy
5. the described antioxidant composition of claim 4 is characterized in that preparing according to the method that may further comprise the steps: (a) add ethanol with the ultimate density that is not less than 40 (w/w) % in the hot water isolate of Oyster and obtain supernatant liquor (step 1); (b) with the gained supernatant concentration to containing 30-45 (w/w) % solids component (step 2); Reaching (c) is that 55-70 (w/w) % is to reclaim throw out (step 3) to wherein adding ethanol to ultimate density.
6. the described antioxidant composition of claim 5 is characterized in that carrying out the method that the preceding pH with supernatant liquor of step (c) transfers to below 3 or 3 and preparing by further being included in.
7. claim 5 or 6 described antioxidant compositions, it satisfies at least one following requirement: (i) the alcoholic acid ultimate density is 40-50 (w/w) % in step 1, (ii) solid component content is 35-40 (w/w) % in step 2, and (iii) alcoholic acid ultimate density about 60 (w/w) % in the step 3.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11513596 | 1996-05-09 | ||
| JP115135/96 | 1996-05-09 | ||
| JP112328/97 | 1997-04-30 | ||
| JP11232897A JP4121583B2 (en) | 1996-05-09 | 1997-04-30 | Antioxidant composition and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1172614A true CN1172614A (en) | 1998-02-11 |
| CN1080295C CN1080295C (en) | 2002-03-06 |
Family
ID=26451522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97113025A Expired - Fee Related CN1080295C (en) | 1996-05-09 | 1997-05-09 | Antioxidant composition and method for production thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5925382A (en) |
| EP (1) | EP0806465B1 (en) |
| JP (1) | JP4121583B2 (en) |
| CN (1) | CN1080295C (en) |
| AT (1) | ATE195547T1 (en) |
| DE (1) | DE69702810T2 (en) |
| ES (1) | ES2148874T3 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11322617A (en) * | 1998-05-07 | 1999-11-24 | Tokiwa Yakuhin Kogyo Kk | Pharmaceutical composition for prevention and treatment of gastric ulcer, containing extract of chicken or oyster |
| WO2006077634A1 (en) * | 2005-01-19 | 2006-07-27 | Japan Clinic Co., Ltd. | Process for producing oyster meat extract |
| JP5679559B2 (en) * | 2011-01-28 | 2015-03-04 | 株式会社渡辺オイスター研究所 | Method for producing antioxidant composition |
| JP5804493B2 (en) * | 2011-04-11 | 2015-11-04 | 株式会社渡辺オイスター研究所 | Method for producing oyster meat extract containing antioxidant substance with high antioxidant power |
| JP5831969B2 (en) * | 2011-09-06 | 2015-12-16 | 株式会社渡辺オイスター研究所 | Method for producing oyster meat extract containing antioxidant substance |
| SG192735A1 (en) | 2011-04-11 | 2013-09-30 | Watanabe Oyster Lab Co Ltd | Method for producing oyster meat essence containing large amount of antioxidants having high antioxidative power and high orac value |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6110515A (en) * | 1984-06-25 | 1986-01-18 | Nippon Kurinitsuku Kk | Substance having blood platelet coagulation suppressing activity |
| JPH0629192B2 (en) * | 1984-09-11 | 1994-04-20 | 日本クリニツク株式会社 | Lithium concentration enhancer |
| JPS61139346A (en) * | 1984-12-12 | 1986-06-26 | Nippon Kurinitsuku Kk | Feed for domestic animal and domestic fowl |
| JPH0653668B2 (en) * | 1986-03-07 | 1994-07-20 | 日本クリニツク株式会社 | Composition for treating schizophrenia |
| JPH0653053B2 (en) * | 1986-04-28 | 1994-07-20 | 日本クリニツク株式会社 | Low molecular fraction in oyster meat |
| JPH06172123A (en) * | 1992-12-10 | 1994-06-21 | Mikimoto Pharmaceut Co Ltd | Antioxidant |
| JPH07102252A (en) * | 1993-10-05 | 1995-04-18 | Mikimoto Pharmaceut Co Ltd | Antioxidant |
-
1997
- 1997-04-30 JP JP11232897A patent/JP4121583B2/en not_active Expired - Lifetime
- 1997-05-07 EP EP97107550A patent/EP0806465B1/en not_active Expired - Lifetime
- 1997-05-07 AT AT97107550T patent/ATE195547T1/en not_active IP Right Cessation
- 1997-05-07 ES ES97107550T patent/ES2148874T3/en not_active Expired - Lifetime
- 1997-05-07 DE DE69702810T patent/DE69702810T2/en not_active Expired - Fee Related
- 1997-05-07 US US08/852,172 patent/US5925382A/en not_active Expired - Lifetime
- 1997-05-09 CN CN97113025A patent/CN1080295C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1080295C (en) | 2002-03-06 |
| ATE195547T1 (en) | 2000-09-15 |
| DE69702810T2 (en) | 2001-02-22 |
| EP0806465B1 (en) | 2000-08-16 |
| EP0806465A1 (en) | 1997-11-12 |
| JP4121583B2 (en) | 2008-07-23 |
| ES2148874T3 (en) | 2000-10-16 |
| US5925382A (en) | 1999-07-20 |
| DE69702810D1 (en) | 2000-09-21 |
| JPH1036275A (en) | 1998-02-10 |
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